The Pros & Cons of Being aRemote Team (& How We Do It)

Working remotely has a lot of advantages, but it’s far from perfect. Here’s what we’ve learned in our journey as a remote team.

Headphones.

They were practically all I could see.

An ocean of big, round, silver headphones attached to silent, focused faces that hadn’t said a word all day.

When my last company grew big enough, we did what startups in New York were supposed to do.

We rented a big, trendy SoHo loft to give our team a headquarters.

It was a wide open floor plan that gave everyone the opportunity to talk to one another and collaborate seamlessly.

It was an opportunity that few actually took.

At around 9AM, employees would wander into the office, pour themselves a cup of coffee, sit down at their desks, put on those big silver headphones and get to work.

And they’d stay in that position for the whole day.

Headphone City

We were productive, and we got along really well, but anyone looking at the scene above would see an army of headphones getting little benefit from sharing a physical space.

When I started Groove, I decided to go in a different direction.

To forsake the office and build a remote team.

I still wonder if it was the best decision, but regardless, it’s the one I made.

Many months later, I’ve learned a lot about remote work.

About working from a home office, managing a remote team and building a business where the employees hardly ever see one another.

Below are some of the most important lessons I’ve learned.

If your team is already a well-tuned distributed machine, you’ll already know about most or all of these lessons, because like us, you’ve learned them the hard way.

But if you’re at the same crossroads I was at in choosing which direction to go, or if you’re looking for tips on being a more efficient, cohesive and productive remote team, then this post is for you.

The Good: Pros of Running a Remote Team

1) We have access to more and better talent, faster.

When it was time to start hiring, I tried to contain my initial push for developers to the area surrounding Newport.

Asking for referrals

Unfortunately, I couldn’t find anyone with the skills, experience and intangibles that I was looking for.

As soon as I opened up my search to include the rest of the country, I found the right employees very quickly.

Our first two engineering hires were made within the next few weeks, and they’re still with Groove today.

We now have team members in Rhode Island, Maryland, North Carolina, Colorado, Utah and Illinois, with part-time help from Bulgaria, Russia and a few other parts of the world, depending on what we’re working on.

And averaging one to three weeks, the searches for those team members were relatively short compared to the six-week-or-more recruiting campaigns we’d undergo to hire a single employee at my last startup.

2) Our employees have lives outside of work.

But our team is happy, and one of the things we all appreciate is the freedom to spend time doing the things that are important to us beyond our jobs.

We have a 15-minute team call every Monday morning that everyone attends. That’s when we make sure that we’re all on the same page about accomplishments from the previous week, and goals, deliverables and challenges for the coming week.

Of course, there’s a ton of collaboration that happens outside of that weekly call, but that’s our only scheduled meeting.

Aside from that, our team works when and where they want to. And we all have other commitments.

Most of us are married or in serious relationships.

Two of our team members have babies (read: second full-time jobs).

Another is engaged to a nurse whose schedule changes every week. Their lives are made a lot easier by the fact that he’s able to work the same hours as her (sometimes, that means early mornings, evenings or weekends) and get time off when she does (usually weekdays).

Personally, I love living next to the ocean. On more than one occasion, I’ve stopped what I was doing, grabbed my board and headed out for some mid-day surfing.

Would all of these things be possible if we worked in an office?

Sure, there are a lot of people who make it work.

But not spending two hours per day commuting, and having the flexibility to work when you prefer sure does make it easier.

15five for staying on top of our team’s happiness and challenges: $49/month.

Pivotal Tracker and Trello for project management: $23/month (though we would certainly use these from an office, too).

Every dollar we save on rent is a dollar we can reinvest in the growth of the business and our employees.

The Bad: Cons Of Running a Remote Team

1) A great startup employee doesn’t necessarily make a great remote startup employee.

While the talent pool certainly gets bigger when you’re hiring from around the world, your hiring needs also change drastically.

We can’t just hire good startup employees, because we’ve found that that simply isn’t enough.

Most people don’t have the organization, focus and motivation to be productive working remotely.

It’s not that they can’t. It’s just that they haven’t had to.

Successfully working from home is a skill, just like programming, designing or writing. It takes time and commitment to develop that skill, and the traditional office culture doesn’t give us any reason to do that.

We had some early hires — very talented people — not work out, only because they had never worked remotely before and we were unsuccessful at helping them develop that skill.

Now, we don’t just look for good startup employees, but we look for good startup employees with experience working remotely.

Everyone on our team has either worked on a distributed team before, or been a freelancer or entrepreneur in the past.

2) Company culture takes a hit.

There’s a lot more to startup culture than having an office. At the end of the day, culture is about shared values and goals.

But having everyone in one place makes it a lot easier to build that culture.

The more exposure team members have to each other, the more developed and defined that culture becomes.

Simply by virtue of being remote, that exposure is necessarily limited.

We’ve done a pretty good job at working on culture through close contact in HipChat, team culture exercises and ensuring that new employees are a good fit through trial periods before we hire.

An Average Hipchat Afternoon

But it’s still, and I suspect always will be, a challenge.

3) Communication gets harder.

With team members in different time zones and on different schedules, there are very few times when everyone is available.

Most of the time, this isn’t an issue.

Outside of our weekly call, our team primarily uses HipChat to talk, as it keeps everything in one place and saves chat messages for when a user gets back online.

But sometimes, you need an answer now.

Maybe a customer needs an urgent fix and the developer you need is coding away in full-screen.

Maybe there’s a question about a blog post that needs to go out today, but the only person who can answer it is three time zones away and won’t be up for another two hours.

In an office, if someone isn’t responding to an email, it’s easy enough to stop by their desk and get what you need.

But for everything else, it means we have to be organized and diligent about tracking what we need from each other. And if getting that information or deliverable is an obstacle, we need to be able to switch tasks until we can get it.

It’s not the most efficient system.

While I think there’s a net positive impact on productivity from working remote, the communication barrier can, and sometimes does throw a wrench in the gears.

4) It’s (practically) impossible to transition to an office.

At this point, whether or not I was wrong about going the remote route doesn’t really matter.

Switching to an office-based team would mean either a) moving everyone to one place, or b) laying off the team and starting over.

We have an amazing team, and they’ve got deep roots all over the place.

Neither of those options are on the table now, nor will they ever be.

So in the practical sense, the fact that we can’t switch isn’t a challenge, since it’s not happening.

But it’s a challenge in that I always wonder whether it was the right move.

Would we have grown faster if our team was in one place?

Would we have been taken more seriously by press and potential business partners?

Would we have been more productive and efficient by working elbow-to-elbow?

We’ll never know.

We’ve Still Got (Remote) Work To Do

Although we’ve tackled a lot of the hardest challenges of working as a remote team, and reaped many big rewards from it, I’d hesitate to call us a remote success story… yet.

We’ve still got work to do, and much of that revolves around developing and protecting our culture and collaboration as we grow.

Some of the ways we’re going to be doing that include:

Retreats to bring the whole team together in person (it’s crazy to me that I’ve never actually met a couple of the people I work with).

More defined systems for onboarding new employees to our remote "office."

Hiring employees in more time zones to improve our support coverage and development cycle.

I hope that our experiences help you make up your own mind about whether remote is the right way to go for your business, and if you’re a remote team, I hope you’ve learned something new.

This is an important topic to Groove, and we’ll keep writing about it as we learn new things and grow our team.